Your Comprehensive Guide to Packing a Carry-On Like a Pro

I spend a lot of time traveling, be it for business or pleasure. Over the years, I’ve refined the packing process into something of an art form, but let me tell you, it has taken a lot of trial and even more errors to get here. I’ve made dozens of rookie mistakes, like the time I forgot to pack my passport, but I’ve also gained dozens of insider tips along the way; like knowing turbulence can be felt most in the back of the aircraft and above the wings (this totally changed my opinions on preferred seating).

I’ve learned when to roll with the punches — and when to use one of two packing techniques to get the most out of my carry-on luggage space. Now more than ever, airlines are cracking down on how much you can take on-board, while our list of essentials grows by the day. Learning how to pack a carry-on bag that can meet all your needs is a life skill worth learning, and could save the day if you find yourself on a cancelled flight, or traveling with expensive goods like laptops or tablets.

So, what goes in checked baggage versus a carry-on? This might sound obvious, but many people mistake carry-on as an opportunity to skip the carousel lines, and take all their luggage on-board with them. This is completely wrong and is actually poor travel etiquette. The correct method is to check the bulk of your items underneath the plane in the cargo area and to literally “carry on” only those essential items that make your travel experience easier and more entertaining.

Generally, passengers can take two pieces of carry-on, such as a carry-on suitcase and a carry-on bag, however space is limited and actively enforced. If this is your first flight, expect to see a booth when you check-in that can weigh the mass of your carry-on, and that also allows you to verify the dimensions. For carry-on, the shape of the luggage is even more critical than the mass as you must meet the health and safety requirements, and be able to pack your luggage into an overhead compartment neatly.

If you want to know how I pack a carry-on bag, and what goes into my essential travel kit, then keep reading. I’m going to give you a step-by-step guide on what to pack, how to pack, and what to leave at home or under the aircraft so that you can fly with total peace of mind!

Identifying Your Carry-On Luggage

You can tell a lot about a man and his carry-on choices; are you the guy who takes nothing onboard but his phone and headphones? Or are you the guy who maximizes his (and his wife’s) allocated carry-on? It might surprise you, but an airline friend revealed to me that men who have less carry-on are more likely to be offered an upgrade. Not only is their minimal luggage appealing to cabin crew, but a man who has a minimal amount of carry-on appears more refined and responsible. So, next time you think about what to pack, perhaps remember that more really is less!

Rule number one: always check with your airline before making any decisions on what to pack. Airlines all have varying guidelines. This also means that if your journey includes multiple airlines, you will need to ensure you meet the carry-on requirements for both airlines before departing, or you could end up paying hefty fines or being asked to leave some items behind. Furthermore, if you are carrying obscure items, such as a guitar, always call ahead even if you read somewhere that it’s fine to take.

You can check the airline's FAQ page for the basic outlines of what you are entitled to take; check for the measurements of the largest bag you can bring, how many bags in total you are allowed, and what are the exceptions. Generally, I fly with the same company to build on travel incentives, but an overlooked bonus is that if you fly with one commercial airline, you can buy a carry-on bag that meets their needs, so you don’t always have to switch up your protocol per flight.

The Airplane Carry-On

When it comes to your basic, TSA-approved carry-on bag, the Away Carry-On (not to be confused with it’s slightly bigger brother, the “Bigger Carry-On”) has plenty of room to fit enough stuff while keeping inline with almost airline’s size requirement. Available in an array of colors, you can opt for classic black with your monogrammed initials, or go bold and get the sky blue, blush pink or even the bright white. If you want to really up your travel game, swap out your basic bag for their new aluminum carry-on so you can look back at every little ding and be reminded of where your travels have taken you.

All Away Carry-On styles come with a TSA-approved ejectable battery so you don’t have to worry about getting down on your hands and knees and searing the airport floor for a plug to finish your Insta story — or work, whatever. The battery has enough juice to charge an iPhone five times (yes, that is five full times) and is easily removable to comply with whatever your airline wants you to do with it today. The TSA-approved lock means handsy handlers can’t take a look inside and the hidden snap-in laundry bag means you don’t have to mix your cleans with your dirties.

This brings me to my next important tip: just as every man’s needs are different, so too is every trip. Just because a bag or a list worked for a weekend away, does not mean it’s sufficient for a business trip or to plan your vacation around. While the ideal carry-on bag is durable, easy to carry, and protective, it likely will vary depending on what the purpose of your trip is; therefore, I’m going to show you how to pack for different trips and durations.

The Weekend Carry-On

The most exciting option is, of course, the weekend getaway carry-on bag; this is the one you can pack with all your favorite gadgets and gizmos, safe in the knowledge that you can turn off work. The ideal vacation bag is proportionate to the length of your vacation; the longer you go, the larger your bag can be (so long as you remain in the carry-on requirements). One of my favorite go-to vacation carry-on bags is the Michael Kors Henry Suede Duffle, because it has tons of space and is comfortable to carry.

If you only ever invest in one carry-on bag, I recommend a duffle bag, as they are super versatile and can carry a lot of items comfortably. Duffle bags are no longer giant black holes; you can find ones with compartments inside, and discreet pocket linings to make the best use of your space. I especially love the duffle bags that have a shoe compartment, as shoes and socks can get funky on the road. This is a great way to keep swimwear or dirty items separate from your regular clothing.

The Business Carry-On

The carry-on I travel with most is the business carry-on; this is the one you need to slim down, especially if you plan to fly first class. A briefcase is a standard choice, but I prefer the modern versions that have a shoulder case (so you can sling it over your shoulder for comfort or ease of carrying if you need to make a run for your departure gate). My business carry-on also needs to have lots of pockets, so that I can safely store my phone, wallet, keys, and passport, etc.

A faithful business carry-on bag that serves me well is the LeDaveed Slim Briefcase. I love this bag because it while it looks sleek and clean, it was built for tech. There’s well proportioned padded compartments for my laptop and accessories, cubby pockets for chargers and headphones, and two-way riri zippers unzip extra wide to allow for easier load-in. There is a detachable shoulder strap for easing a heavy load, and it can be carried to look like a traditional briefcase. It also has a slim profile and luggage attachment, making it easy to slide on top of a carry-on suitcase if I double up.

The Casual Carry-On

Finally, we have the casual carry-on bag. This is a general hold-all that some guys will find useful for flying, but typically you will lean on either the vacation or business necessities first. The causal carry-on is usually covered in a simple backpack and is fitted with lots of small knocks for all your essentials. The purpose of your casual carry-on is to minimize space and create a comfortable travel companion for your most basic of needs.

When looking for a backpack, quality means a lot. You want to ensure your backpack is well structured and has a lot of padding and organizational space. Backpacks tend to get knocked around and sat on in a crunch. Backpacks have also come a long way since school and can be incredibly tech motivated. I love the Witzman shoulder-duffle bag, as it can be worn three ways and has lots of storage space, including a large hidden front pocket, perfect for all your important travel items.

The Dopp Kit

If you’re hopping on a plane, chances are you will need a bag beyond that quart-sized, zip-top plastic baggie that’s required to go through the x-ray. If you’re just jumping in a train or car for the weekend, you’ll ditch the baggie and opt for something a little more put together. Either way, you’re looking at a dopp kit — the bag that holds all those mini soaps, shampoos and whatever else you’ve got going with you to stay clean and hygienic while you’re traveling.

This classically handsome dopp kit from Hook & Albert is a favorite for its ability to fold down flat on either side while it’s sizable main compartment has a firm opening (that stays open) with an interior pocket for smaller items. Everything on the interior of this bag is also lined with water-resistant nylon, which means it’s all party on the outside, business on the inside.

How Much Should I Pack for an Overnight Trip?

Now that you know what you can carry, and what you are going to be packing, it’s time to ask one of the most important questions of all: how much should I pack for an overnight trip? By understanding how much to pack for one night, you can essentially multiply your load per your total night stay to get a reasonable estimate of how much to pack for your trip. While you might be asking what an overnight trip has to do with your flight, understand that delays can and will happen.

Tip 1: Be objective: the length of your trip determines how much to pack in a carry-on, of course, but there are some ways to reduce your luggage on both short-haul and long-haul flights. I love to make a list of everything I need and want to take with me; “need” being items I must travel with, and “want” being those things I desire. The goal of a master list is to get everything on paper so you can cut back on items to find the right balance.

Tip 2: Start to pull all of the items you want to carry-on into one area and see how much space they physically take up. You do not need to pack your carry-on bag now. The goal is to estimate how much you have and to confirm you have everything you need. I find seeing the items in front of me will confirm if I really need to take something with me, like my MacBook, or if I can leave something in the luggage space, like a book (which I can read as a Kindle version from my phone).

Tip 3: Account for emergencies. This is a big step that many men often overlook. If your flight is late, do you have items you need for later in the day? For example, do you have dietary needs or do you take medication? Ensure you pack these items with their correct prescriptive information into your carry-on and be prepared to declare these items as you travel. Always plan for the worst-case scenario, and assume your travel plans need a 24-hour back up plan.

The bonus of your master list is that once you finalize the list items, you can pack this in your luggage, along with a description of who you are and your address, so that should you leave it on a flight, or on a terminal floor, it can be returned quickly. Also, when re-packing your items on the other side, you’ll have a solid game plan. Usually, traveling tires us out, and you’ll be thankful to have done all the prep work before departing on your trip.

Some items to consider packing in your carry-on include:

Work or school items: If your flight is 4-6 hours, this could be an excellent opportunity to get some work done before you arrive. Many flights now have Wi-Fi access, making your cabin a personal office space. Consider your laptop or tablet, a charger, and save the important information offline (as not all aircraft have Wi-Fi).

Entertainment: In its most basic form, you can bring a book or pick up a newspaper in the lobby, but I prefer to fly with tech. Headphones go a long way; I download podcasts and make sure I have a music playlist saved ahead of time. If it’s a long flight, I will download a few movies in an app to watch via my MacBook.

Medications and toiletries: Obviously, don’t forget any essential medications. I also like to travel with a few grooming essentials, such as Burt's Bees All-Natural SPF15 Moisturizing Lip Balm, Nivea Men Creme (which works for hands as well as face and body in a pinch) and Eau Thermale Avène Thermal Spring Water Face Mist, all in travel size, as flying is dehydrating. I also like to pack a few snacks that meet TSA requirements, for a quick pick-me-up.

Finally, you may wish to bring something to help you sleep. Generally, I don’t recommend these items if it is an 8-hour flight or less. Eye masks, ear plugs, inflatable neck pillows, and so on, can be cumbersome and beg to be forgotten. Instead, I prefer to wear layers of clothing I can take off and repurpose into a neck rest, and put back on at the end of my flight so that I don’t take up valuable carry-on space. Once you get in the air, you won’t need much of this stuff if you have sufficient entertainment.

Identifying Common Carry-On Problems

When traveling, it’s important to identify when common carry-on problems are occurring so you can prevent a bigger travel catastrophe. Below is a quick checklist of the common carry-on problems I have seen or experienced firsthand. Remember, this is not a complete list, and you should always be on the lookout for possible problems, but it should steer you in the right direction. In many cases, just being aware of a problem is enough to prevent it from happening.

Failing to make carry-on items accessible: Nothing puts a damper on your day like getting to a checkpoint and realizing that while you’ve packed your bag like a maestro, you can’t actually get to what you need. Sometimes, you need to forfeit space in honor of functionality. This means packing your passport and wallet, for example, near the front or top, so that you don’t have to unpack everything else around them. Sounds obvious, but it does happen.

Failing to plan for the worst: As mentioned, flights can and do change, and your carry-on can quickly be your bug-out bag. This means it needs to be able to support you for 24-hours, or longer, depending on the seasons and when you are flying. Carry cash, medications, and other essential items in your carry-on to make delays comfortable and safe. Increase these with the risk factor; traveling in winter, during known snow storm seasons, for example, means taking extra precautions.

Failing to protect your carry-on: From protective cushioning to the risk of theft, carry-on luggage contains our most personal items for a good reason; we often don’t want those valuables or sensitive items to go beneath the plane and out of our view. Consider buying a small TSA-approved lock set to secure your carry-on bag from thieves, but without preventing agents from approving you to fly. I’ve already factored in protective gear into your carry-on bag options above, so you are ready to go.

Failing to provide sufficient entertainment: While a great carry-on bag covers all the groundwork of what you need, many people don’t bring enough entertainment. Nothing is worse than being 30,000 foot in the air with nothing to do. Make sure you bring adequate entertainment; this means looking at how long your flight is, and budgeting for delays and time on the ground. You don’t want to read all your book before you take off and be left with nothing to do.

Finally, failing to dress correctly: I want to include this in carry-on luggage because what you wear is part of your pat-down. When flying, you should always wear light layers to acclimatize to the many different environments travelers experience; terminals, air cabins, day/night, all factor into varying needs and you’ll be thankful when you can customize your outfit. Use your waist or shoulders to carry layers, and don’t take up precious space in your bag.

Passing TSA in 3 Simple Steps

One of the biggest hurdles we face when flying with carry-on is TSA; these are the people who pat you down and check your luggage to ensure the safety of all passengers. Since 9/11, airport restrictions have become infamous, and meeting TSA requirements is mandatory. The TSA can ban you from flying, so it’s best to follow the rules and pack a carry-on bag that allows a seamless and stress-free TSA experience. You can do this by following some basic rules:

Contact the airport ahead of departure to find out what the TSA rules are for your area, and for the airport you will be returning from. While many of the rules remain the same, some airlines may have extra precautions depending on when and where you travel. For example, going to a city during a major festival will see more enforcement of carry-on rules.

Pack your liquids correctly, and double check that all your items meet the size limits before packing your carry-on. Liquid items should be packed in a clear, quart-sized plastic bag, such as a zip-lock bag, and must be declared when going through TSA. Look out for that stray water bottle you bought in the main terminal to remain compliant when traveling.

Follow the 3-1-1 rule. If you are traveling domestically, a U.S. passenger can carry three bottles containing no more than 3.4 ounces (or 100ml) of liquid. Larger liquids can be stored in your checked luggage.

How to pack liquids in a carry-on: Remember, as you won’t be allowed to take most liquids through security, you need to be aware of what you pack. You can find out how to pack liquids specific to your trip by contacting the Bureau of Consular Affairs, the Transportation Security Administration (TSA), and the airline you are traveling with; each of these departments aim to work together, but may have their own rules you need to follow. I recommend keeping their contact info handy.

Here are some grooming FAQ’s people often ask me:

Can I pack a razor in my carry-on? Amazingly, yes! You can pack disposable razors in your carry-on luggage. However, this is the only kind of razor you can bring. You can purchase a travel size can of shaving gel, but this will use up one of your liquid allowances. The same applies for nail clippers (which must be less than 4 inches).

Can I pack cologne? I recommend sample size or small grooming products, such as a balm or oil cologne, which will take up less liquid space. A standard bottle of cologne is too large for your carry-on and will need to be trashed. Instead, consider this subtle oil roller cologne from Malin+Goetz, which can be applied discreetly, and comes in a travel friendly size. Plus, it's not overpowering, so the folks on the plane won't get turned off if you have a fragrance that doesn't agree with them.

How do you pack toiletries? The broad answer is only pack what needs to be used during the trip, is TSA-approved, is compact, and can be used in multiple locations. Vaseline, for example, is a great balm that can also tidy up stray hairs and rejuvenate eye bags in a pinch. Generally, though, unless you are delayed, expect to freshen up on arrival.

How to Pack Lighter: Folding/Rolling Techniques

As promised, I want to share two techniques I use when traveling. Learning how to pack can often be more important than learning what to pack; remember, what you wear is considered part of your carry-on, so lay out the clothes you want to wear with your items. Now that you have all the items with you and you have determined these are the most important, it’s time to put them in your carry-on bag.

How do you pack a suit in a suitcase? Assuming your suitcase is the correct size, begin by laying out the suit on a flat surface. Take the blazer, and fold the shoulders into the middle to create a column. Fold the pants in half and lay them on top of the blazer. Then fold the blazer and pants together, in half, and lay flat in your carry-on suitcase.

How do you pack a tie? I don’t bother with fancy tie carrying cases as, truthfully, I don’t wear many ties, but they are useful if you have more than five. Otherwise, simply fold the tie in half, and roll it up into a ball like a sock, and place it in a corner or pocket.

How do you fold a dress shirt? Shirts get a bit trickier; it’s best to button the shirt and lay it out flat. Fold the sleeves into the middle of the shirt and then bring the bottom upwards. You can fold the shirt lengthways to make a smaller profile. Lay it flat on top of your suit. You can pack the shirts side-by-side per the width of your suit.

The Rolling Method

For most carry-on items, I love the rolling method: this is where you simply fold larger pieces into a basic rectangular shape (for example, fold a t-shirt’s sleeves inwards), and then roll the item into a tight log that can be packed side-by-side; this method is perfect for boxers, shirts, and even spare socks, which take up a lot of space when left balled up. The rolling method also reduces crinkles, but I do not recommend rolling shirts, suits, blazers, or other items that have a strong structure.

As you are rolling, be sure to use a flat surface, and “iron out” any wrinkles with your hands as you go — this is not a time to rush. If you are rolling a long sleeve shirt, fold the sleeves diagonally across the back of the shirt so that they form an X. If you are folding a collared shirt, unfold the collar. In your checked luggage, place similar items, such as boxers, into gallon-size Ziploc bags for reference.

The Compression Method

I typically only prefer to use the compression method if I’m traveling with sensitive carry-on items, as it creates an inflexible packing process. As the name suggests, you are using compression to get everything into the bag and to hold it in place. This means you can’t really dig for anything once it’s in there, making this limited for carry-on. If I buy an expensive or fragile souvenir, however, I will use the compression method to lock it down.

This method relies on compression packs, such as Lekors travel bags, which you fill with items, and then vacuum the air out of the bag, and pack. You can actually save a lot of space in your carry-on by taking out the air; I recommend this method for carry-on suitcases, as these typically are not brought onboard for their need to be accessible. Bolster delicate items inside compressed shirts to create a 3D barrier.

At the end of the day, we can talk about packing, unpacking, rolling, and generally squeezing every inch out of your carry-on luggage, but unless you get out there and get packing and traveling, you will never figure out what works for you. All my best traveling tips have been learned on the road from real life experiences, and believe me, once you make a mistake once, you won’t make it again! So just remember that traveling is a gateway to experience, and enjoy the ride.

If you’ve ever wondered how to travel in style, or how your favorite celebs arrive looking coiffed and photo-ready, stay tuned! Victor Macias, founder of Male Standard, the authority on men’s grooming, is giving away his best tips and tricks the “every man” needs to travel like a true champ! Your carry-on bag is the gateway to your best travel experience yet! To find out more on how to maintain good skin while flying, check out MaleStandard.com.

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